ISSN:
0170-2041
Keywords:
Carbohydrates
;
Pseudo-sugars
;
Cyclitols
;
Hexopyranoses, 5a-carba-
;
Bicyclo[2.2.1]heptanes, 7-oxa-
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
cis-Hydroxyamination of endo-2-acetoxymethyl-7-oxabicyclo[2.2.1]hept-5-ene (1) under Sharpless conditions affords two positional isomers 3 and 7 of 5-endo-acetoxymethyl-2(3)-exo-hydroxy-3(2)-exo-p-toluenesulfonamido-7-oxabicyclo[2.2.1]heptanes. Cleavage of the 1,4-anhydro ring of the corresponding acetyl derivatives 4 and 8 with 18% hydrogen bromide in acetic acid at 80°C produces several bromodeoxy aminocyclitol derivatives, from which, on hydrolysis or nucleophilic substitution with an acetate ion, the known 2-acet-amido-5a-carba-2-deoxy-α-DL-allo (25) and -gulopyranose tetraacetates (26), and new 3-acetamido-5a-carba-3-deoxy-α-DL-allopyranose tetraacetate (30) have been obtained. Likewise, the new 3-acetamido-5a-carba-3-deoxy-β-DL-talopyranose tetraacetate (39) has been prepared by starting from the exo-isomer 2.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1992199201108
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